通过氮丙环脯氨酰甘氨酸上铜催化的 1,3-偶极环加成反应合成氮杂-1,2,3-三唑-3-丙氨酸。

Aza-1,2,3-triazole-3-alanine synthesis via copper-catalyzed 1,3-dipolar cycloaddition on aza-progargylglycine.

机构信息

Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre-Ville, Montréal, Québec H3C 3J7, Canada.

出版信息

J Org Chem. 2010 Aug 6;75(15):5385-7. doi: 10.1021/jo100957z.

PMID:20583744

Abstract

The parallel synthesis of seven aza-1,2,3-triazole-3-alanine azapeptides of the Growth Hormone Releasing Peptide-6 (GHRP-6) was accomplished via a Cu-catalyzed azide-alkyne [3+2] cycloaddition on an aza-propargylglycine residue anchored on Rink amide resin. Circular dichroism spectroscopy in water demonstrated that azapeptides which possess an aza-1,2,3-triazole-3-alanine residue at the Trp(4) position of the GHRP-6 sequence adopt beta-turn conformations.

摘要

通过在 Rink 酰胺树脂上连接的氮丙啶基甘氨酸残基上进行铜催化的叠氮化物-炔烃 [3+2]环加成反应，完成了生长激素释放肽-6 (GHRP-6) 的七个氮杂-1,2,3-三唑-3-丙氨酸氮杂肽的平行合成。在水中的圆二色性光谱表明，在 GHRP-6 序列的色氨酸（4）位置具有氮杂-1,2,3-三唑-3-丙氨酸残基的氮杂肽采用β-转角构象。